Nitrogenous condensation product from 1.2-alkylene imines



Patented May 20, 1941 S PATENT OFFICE NITBOGENOUS CONDENSATION PRODUCT FROM LZ-ALKYLENE IMINES Heinrich Ulrich haten-on-the-Rhine mesne assignments,

Corporation, New York,

Delaware and Karlhugo Kuespert, Ludwigsermany to General asslgnors, by Aniline & Film N. Y., a corporation or No Drawing. Application January 21, 1939, Serial No. 252,120. In Germany January 25, 1938 18 Claims. (Cl. 260-239) The present invention relates to a new nlt1'08- enous condensation products and a process of producing same.- L Y In the copending application Ser. No. $3,767, filed on August 1. 1936, in the name of Heinrich Ulrich, one oi! the inventors of thepresent invention, there is described a process for the production of nitrogenous products which consists in causing alkylene imines to react with organic compounds containing at least one group capable of reacting with basic compounds. The alkylene imines may be employed in the monomeric or polymeric form. The reaction 01 alkylene imines with-"aliphatic isocyanic acid esters is also described, inter alla.

We have now found that very valuable nitrogenous condensation by using saturated aliphatic isothiocyanic acid esters instead of the aliphatic isocyanic acid esters. Among suitable isothiocyanic acid esters there may be mentioned for example methyl, ethyl, propyl, isopropyL-normal-butyl, isobutyl and octyl mustardoils. The alkylene imines to be employed comprise monomeric 1.2-alkylene imines as well-as 1 .2-alkylene imines merization.

The reaction the products are similar said application-Set. No. 93,767.

The following; example will further illustrate the nature of this invention but the invention is not restricted to this example. The parts are by weight.

of any desired degree of polyconditions and the properties oi Example polymeric ethylene imine are inwith about 100 parts of butyl a white mass is formed which is soluble with difficulty 40 in water and more readily soluble in hot alcohol. The'product may be used for rendering fibrous materials water-repelling.

What we claim is: I

l. The process of producing nitrogenous products. which comprises condensing a 1.2-allrylene imine with a saturated aliphatic isothlocyanlc acid ester.

2. The process ucts, which comprises condensing a imine with butyl mustard 3. The process of producing nitrogenous products, which comprises condensing a polymerization product of 1.2-alkylene imine with a saturated aliphatic isothiocyanic acid ester.

of producing nitrogenous prod- 4. The process of producing nitrogenous products, which comprises condensing a polymerization product of 1.2-alkylene imine with butyl 7 .mustard oil.

products are also obtained polymer'ization products 0!- to those described in the v 5; Nitrogenous condensation products from 1L2-alkylene imines andsaturated aliphatic isothiocyanic acid esters.

-6. Nitrpgenous condensation products from LZ-alkylene imines' and butyl mustard oil.

7. Nitrogenous condensation products from polymerization products of 1.2-alkylene imines and saturated aliphatic isothiocyanic acid esters.

8. Nitrogenous condensation products from polymerization products of 1.2-alky1ene imines and butyl mustard oil.

9. The process of producing nitrogenous products which comprises condensing ethylene imine with a saturated aliphatic isothiocyanic acid ester.

10. The process 0 products which comprises condensing ethylene imine with butyl mustard oil.

11. The process of producing nitrogenous products which comprises'condensing polymerization product of ethylene imine with a saturated aliphatic isothiocyanic acid ester.

12. The process of producing nitrogenous products which comprises condensing polymerization product of ethylene imine with butyl .mustard oil.

13. Nitrogenous condensation products from ethylene imine and saturated aliphatic isothiocyanic acid esters.

14. Nitrogenous condensation products from ethylene imine and butyl mustard oil.

15. Nitrogenous condensation products 'from ethylene imine and I polymerization product of saturated aliphatic isothiocyanic acid esters.

16. Nitrogenous condensation products from polymerization product of ethylene imine and butyl mustard oil. i

17. The process of producing nitrogenous products which comprises condensing amember 4 01 the group consisting of 1.2-alkylene imihes 1.2 -alkylene member of products o! 1.2-alkylene ted aliphatic isothiocyanic and polymerization imines with a satura acid ester.

18. Nitrogenous condensation products from a the group consisting of 1.2-alkylene imines and polymerization products of 1.2- alkylene imines and saturated aliphatic isothio- I cyanic acid esters.

HEINRICH ULRICH. KARLHUGO KU'ESPERT.

i producing nitrogenous 

